"but sometimes the software isn't up to date."
if you ever get software from outside sources
you would need to check the license of the software to ensure its libre
also its a good idea to compile the program yourself
as this is much more secure and will ensure you have the absolute latest
version
"This makes me wonder, if there is a way for Trisquel to do a sweep to check
if my installed software is Libre?"
currently only for the deb packages
there is a program call vrms(virtual Richard stallman)
that lists any deb packages installed that are non-free by the Debian free
software guidelines
but this program is controversially and quite incorrectly named as it goes on
Debians free software guidelines not the fsf's and is inconsistent with RMS's